Novel Polymerization Method of Wholly Aromatic Polyamides Polycondensation between Isophthaloyl-diimidazolide and Aromatic Diamines

Three active p-aminobenzenesulfonic acid derivatives, 1-@-aminobenzenesulfony1)imidazole (4a), 1-@-aminobenzenesulfony1oxy)benzotriazole (4b), and 2-phenyl4@-aminobenzenesulfonyl)-l,3,4-oxadiazoline-5-thione (4c) were synthesized by reacting p-isocyanatobenzenesulfonyl chloride (1) with stoichiometrical quantities of water in the presence of dibutyltin didodecanoate and subsequently with imidazole, 1-hydroxybenzotriazole and 2-phenyl-l,3,4oxadiazoline-5-thione, respectively. The self-polycondensation of 4 ac, leading to poly@-benzenesulfonamide) (7, was carried out in solution using polar aprotic solvents, N-methyl-2-pyrrolidone WMP) and hexamethylphosphoric triamide (HMPA), and acidic media, dimethyl sulfoxide (DMSO) and m-cresol, with or without an appropriate acid catalyst or acid acceptor under mild conditions. Poly@-benzenesulfonamide) having the highest reduced viscosity of 0,14 dl . g-' was obtained almost quantitatively from 4c by using m-cresol as a solvent without any acid catalyst and acid acceptor at 25 "C. The polymers are soluble in polar aprotic solvents such as NMP, HMPA and DMSO and in aqueous sodium hydroxide. These poly@-benzenesu1fonamide)s are less thermally stable than completely aromatic polyamides, because the initial weight-loss started at 250 -350 "C. Aminolysis of three benzenesulfonic acid derivatives, 1-benzenesulfonylimidazole (5 a), 1-benzenesulfonyloxybenzotriazole (5 b), and 2-phenyl-4-benzenesulfonyl-l,3,4oxadiazoline-5-thione (5c), with the same leaving groups was also carried out as a model reaction of self-polycondensation to determine the reaction conditions.

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Novel Polymerization Method of Wholly Aromatic Polyamides Polycondensation between Isophthaloyl-diimidazolide and Aromatic Diamines

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Novel synthetic approach to poly(p‐benzenesulfonamide): Self‐polycondensation of active p‐aminobenzenesulfonic acid derivatives under mild conditions

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